LiOOt-Bu as a terminal oxidant in a titanium alkoxide-mediated [2+2+2] reaction cascade

[Display omitted] LiOOt-Bu is an effective oxidant for converting the penultimate organometallic intermediate generated in a titanium alkoxide-mediated [2+2+2] reaction cascade to an allylic alcohol. Oxidation of the presumed allylic titanium species is highly regioselective, providing direct access...

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Veröffentlicht in:Tetrahedron letters 2015-06, Vol.56 (23), p.3557-3559
Hauptverfasser: Kim, Wan Shin, Aquino, Claudio, Mizoguchi, Haruki, Micalizio, Glenn C.
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Sprache:eng
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Zusammenfassung:[Display omitted] LiOOt-Bu is an effective oxidant for converting the penultimate organometallic intermediate generated in a titanium alkoxide-mediated [2+2+2] reaction cascade to an allylic alcohol. Oxidation of the presumed allylic titanium species is highly regioselective, providing direct access to substituted hydrindanes containing a primary allylic alcohol. In addition to demonstrating the feasibility of this oxidation process, we document the ability to convert the primary allylic alcohol products to angularly substituted cis-fused hydrindanes.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2015.01.029